Issue 17, 2021

2,4-Diamino-6-phenyl-1,3,5-triazin-1-ium nitrate: intriguing crystal structure with high Z′/Z′′ and hydrogen bond numbers and Hirshfeld surface analysis of intermolecular interactions

Abstract

2,4-Diamino-6-phenyl-1,3,5-triazine-1-ium nitrate (LH)(NO3) crystallises in the triclinic centrosymmetric space group P[1 with combining macron] with an intriguing high number of crystallographically unique salt-like adducts (Z′ = 8) and a total number of ionic species (Z′′ = 16) in the asymmetric unit. The organic cations and nitrate anions are combined into two similar H-bonded neutral tapes strengthening by 20 unique NH⋯O and NH⋯N hydrogen bonds each. Hydrogen bonds are ordered into a repeated sequence of homo- and hetero-synthons, R22(8)R33(10)R22(8)R22(8)R24(8)R33(10) as ring motifs. The paired cations form R22(8) ring motifs through base pairing of N–H⋯N hydrogen bonds. All other patterns include both cations and anions. In the crystal structure, the compromise between the tapes rigidity provided by the multiple directional H-bonds within the tapes and packing preferences is reached through the restricted internal rotation about the C–C bond joining the phenyl and triazine cycles in the 2,4-diamino-6-phenyl-1,3,5-triazine-1-ium cations. The decisive impact of NH⋯O(N) hydrogen bonds in the crystal stability and distribution of other types of intermolecular interactions was estimated by Hirshfeld surface analysis. The undertaken CSD overview for the metal-free L-based crystals reveals the exclusivity of the title compound from the viewpoint of the high reported Z′/Z′′ values and the number of unique hydrogen bonds.

Graphical abstract: 2,4-Diamino-6-phenyl-1,3,5-triazin-1-ium nitrate: intriguing crystal structure with high Z′/Z′′ and hydrogen bond numbers and Hirshfeld surface analysis of intermolecular interactions

Supplementary files

Article information

Article type
Communication
Submitted
04 3 2021
Accepted
25 3 2021
First published
16 4 2021

CrystEngComm, 2021,23, 3099-3108

2,4-Diamino-6-phenyl-1,3,5-triazin-1-ium nitrate: intriguing crystal structure with high Z′/Z′′ and hydrogen bond numbers and Hirshfeld surface analysis of intermolecular interactions

N. Caimac, E. Melnic, D. Chisca and M. S. Fonari, CrystEngComm, 2021, 23, 3099 DOI: 10.1039/D1CE00313E

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